1H-Azepine-1-carboxylic acid, 5-azidohexahydro-6-hydroxy-3,4-bis(phenylmethoxy)-2-[(phenylmethoxy )methyl]-, phenylmethyl ester, (2S,3R,4R,5S,6R)-

Base Information

• Chemical Name: 1H-Azepine-1-carboxylic acid, 5-azidohexahydro-6-hydroxy-3,4-bis(phenylmethoxy)-2-[(phenylmethoxy )methyl]-, phenylmethyl ester, (2S,3R,4R,5S,6R)-
• CAS No.: 848909-02-4
• Molecular Formula: C36H38N4O6
• Molecular Weight: 622.721
• Mol file: 848909-02-4.mol

Synonyms:

Chemical Property of 1H-Azepine-1-carboxylic acid, 5-azidohexahydro-6-hydroxy-3,4-bis(phenylmethoxy)-2-[(phenylmethoxy )methyl]-, phenylmethyl ester, (2S,3R,4R,5S,6R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1H-Azepine-1-carboxylic acid, 5-azidohexahydro-6-hydroxy-3,4-bis(phenylmethoxy)-2-[(phenylmethoxy )methyl]-, phenylmethyl ester, (2S,3R,4R,5S,6R)-

There total 2 articles about 1H-Azepine-1-carboxylic acid, 5-azidohexahydro-6-hydroxy-3,4-bis(phenylmethoxy)-2-[(phenylmethoxy )methyl]-, phenylmethyl ester, (2S,3R,4R,5S,6R)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 64.0%

(1R,4S,5R,6S,7R)-5,6-Bis-benzyloxy-4-benzyloxymethyl-8-oxa-3-aza-bicyclo[5.1.0]octane-3-carboxylic acid benzyl ester (848909-01-3) → (2S,3R,4R,5R,6S)-6-Azido-3,4-bis-benzyloxy-2-benzyloxymethyl-5-hydroxy-azepane-1-carboxylic acid benzyl ester (848909-04-6) + (2S,3R,4R,5S,6R)-5-Azido-3,4-bis-benzyloxy-2-benzyloxymethyl-6-hydroxy-azepane-1-carboxylic acid benzyl ester (848909-02-4)

Guidance literature:

With sodium azide; ammonium chloride; In water; N,N-dimethyl-formamide; at 90 ℃;

DOI:10.1016/j.tetasy.2004.12.005

Reference yield:

(2S,3R,5R)-N-benzyloxycarbonyl-2-benzyloxymethyl-3,4-dibenzyloxy-5,6-didehydro-azepane (724705-55-9) → (2S,3R,4R,5S,6R)-5-Azido-3,4-bis-benzyloxy-2-benzyloxymethyl-6-hydroxy-azepane-1-carboxylic acid benzyl ester (848909-02-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 42 percent / m-CPBA / CH₂Cl₂

2: 64 percent / sodium azide; ammonium chloride / dimethylformamide; H₂O / 90 °C

With sodium azide; ammonium chloride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2004.12.005

Reference yield:

(2S,3R,4R,5S,6R)-5-Azido-3,4-bis-benzyloxy-2-benzyloxymethyl-6-hydroxy-azepane-1-carboxylic acid benzyl ester (848909-02-4) → C36H40N2O6

Guidance literature:

With water; triphenylphosphine; In tetrahydrofuran; at 20 - 60 ℃; for 12h;

DOI:10.1016/j.bmc.2009.06.022

upstream raw materials:

(1R,4S,5R,6S,7R)-5,6-Bis-benzyloxy-4-benzyloxymethyl-8-oxa-3-aza-bicyclo[5.1.0]octane-3-carboxylic acid benzyl ester

(2S,3R,5R)-N-benzyloxycarbonyl-2-benzyloxymethyl-3,4-dibenzyloxy-5,6-didehydro-azepane